Issue 6, 2014

Introduction of polar groups on the naphthalene scaffold of molecular tongs inhibiting wild-type and mutated HIV-1 protease dimerization

Abstract

A new series of naphthalene-based molecular tongs containing polar groups at the 3-position of the naphthalene scaffold was synthesized and its anti-dimerization activity was evaluated against HIV-1 protease. The polar groups were introduced mainly via metal-catalysed cross coupling reactions such as the Buchwald–Hartwig amination, the Sonogashira reaction and the Beller cyanation. Kinetic analyses showed that by introducing specific polar substituents on the naphthalene scaffold the inhibitory activity of molecular tongs against wild-type and mutated HIV-1 proteases is maintained, while increasing their water solubility.

Graphical abstract: Introduction of polar groups on the naphthalene scaffold of molecular tongs inhibiting wild-type and mutated HIV-1 protease dimerization

Supplementary files

Article information

Article type
Concise Article
Submitted
24 Jan 2014
Accepted
12 Mar 2014
First published
17 Mar 2014

Med. Chem. Commun., 2014,5, 719-727

Author version available

Introduction of polar groups on the naphthalene scaffold of molecular tongs inhibiting wild-type and mutated HIV-1 protease dimerization

R. Fanelli, A. S. Ressurreição, L. Dufau, J.-L. Soulier, A. Vidu, N. Tonali, G. Bernadat, M. Reboud-Ravaux and S. Ongeri, Med. Chem. Commun., 2014, 5, 719 DOI: 10.1039/C4MD00032C

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